N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 637343-33-0
• Molecular Formula: C₂₅H₃₆N₄O₁₀
• Molecular Weight: 552.582

Synonyms:

Chemical Property of N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

There total 4 articles about N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

N-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-5-hydroxy-4-((3aS,4R,6R,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (637343-32-9) → N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (637343-33-0)

Guidance literature:

With diphenylphosphoranyl azide; triphenylphosphine; diethylazodicarboxylate;

DOI:10.1055/s-2003-40329

Reference yield:

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (87038-18-4) → N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (637343-33-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / Hg(CN)2 / toluene; nitromethane

2: 75 percent / NaCNBH₃; HCl

3: 95 percent / NaOMe / methanol

4: 78 percent / TsOH

5: 72 percent / PPh₃; DEAD; diphenylphosphoryl azide

With hydrogenchloride; diphenylphosphoranyl azide; sodium methylate; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In methanol; nitromethane; toluene;

DOI:10.1055/s-2003-40329

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → N-[(2R,3R,4R,5S,6R)-4-((3aS,4R,6S,7R,7aR)-4-Azidomethyl-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (637343-33-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / Hg(CN)2 / toluene; nitromethane

2: 75 percent / NaCNBH₃; HCl

3: 95 percent / NaOMe / methanol

4: 78 percent / TsOH

5: 72 percent / PPh₃; DEAD; diphenylphosphoryl azide

With hydrogenchloride; diphenylphosphoranyl azide; sodium methylate; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In methanol; nitromethane; toluene;

DOI:10.1055/s-2003-40329

upstream raw materials:

N-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-5-hydroxy-4-((3aS,4R,6R,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

N-[(2R,3R,4R,5S,6R)-6-Benzyloxymethyl-5-hydroxy-2-methoxy-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

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